Predict the products of the following nucleophilic acyl substitution reactions:

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Interpretation Introduction a) Interpretation: Predict the products of the nucleophilic acyl substitution reactions. Concept introduction: The nucleophilic acyl substitution reaction involved is Base Promoted hydrolysis, not, base catalysed, as shall be seen, because the base - OH is also the nucleophile that adds to the ester and forms part of the product. It participates in the reaction and is not regenerated later [implied in catalysis which does not occur here.] Explanation Steps 1 and 2 result in the rate determining addition of the nucleophile, - OH followed by the non-rate limiting elimination of the leaving group – CH 3 . These two steps, which form the carboxylic acid, are reversible, because the stability a the reactants and products is comparable next, the carboxylic acid is a strong organic acid and the leaving group – OCH 3 is also a strong base, so and acid-base reaction occurs in step 3 to form the carboxylate anion. The carboxylate anion is resonance stabilized, and this drives the equilibrium in its favour... Interpretation Introduction b) Interpretation: Predict the products of the nucleophilic acyl substitution reactions. Concept introduction: To predict the product of a nucleophilic acyl substitution, replace the leaving group of the reagent [viz acetyl chloride ie chloride cl - by the nucleophilic fragment - NH 2 ] to get the actual product. To bit these in to the context of reaction b the following mechanism is devised. Interpretation Introduction c) Interpretation: Predict the products of the nucleophilic acyl substitution reactions. Interpretation Introduction d) Interpretation: Predict the products of the nucleophilic acyl substitution reactions.

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Answer 1

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Organic Chemistry

9th Edition

John E. McMurry

Publisher: Cengage Learning

ISBN: 9781305080485

Solutions

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Section

Answer 2

BuyFind

Organic Chemistry

9th Edition

John E. McMurry

Publisher: Cengage Learning

ISBN: 9781305080485

Solutions

Chapter

Section

Answer 3

Solutions

Chapter

Section

Answer 4

Chapter

Section

Answer 5

Interpretation Introduction

a)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip 1

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Concept introduction:

The nucleophilic acyl substitution reaction involved is Base Promoted hydrolysis, not, base catalysed, as shall be seen, because the base ^-OH is also the nucleophile that adds to the ester and forms part of the product. It participates in the reaction and is not regenerated later [implied in catalysis which does not occur here.]

Explanation of Solution

Steps 1 and 2 result in the rate determining addition of the nucleophile, ^-OH followed by the non-rate limiting elimination of the leaving group ^–CH₃. These two steps, which form the carboxylic acid, are reversible, because the stability a the reactants and products is comparable next, the carboxylic acid is a strong organic acid and the leaving group ^–OCH₃ is also a strong base, so and acid-base reaction occurs in step 3 to form the carboxylate anion.

The carboxylate anion is resonance stabilized, and this drives the equilibrium in its favour...

Answer 6

Interpretation Introduction

b)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip 2

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Concept introduction:

To predict the product of a nucleophilic acyl substitution, replace the leaving group of the reagent [viz acetyl chloride ie chloride cl^- by the nucleophilic fragment ^-NH₂] to get the actual product.

To bit these in to the context of reaction b the following mechanism is devised.

Answer 7

Interpretation Introduction

c)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip 3

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Answer 8

Interpretation Introduction

d)

Organic Chemistry, Chapter 21.2, Problem 5P , additional homework tip 4

Interpretation:

Predict the products of the nucleophilic acyl substitution reactions.

Predict the products of the following nucleophilic acyl substitution reactions:

Organic Chemistry

Solutions

Organic Chemistry